Microbial metabolites of harman alkaloids.

Abstract:

:Several microorganisms showed the ability to transform the harman alkaloids, harmaline (1), harmalol (2) and harman (5). Harmaline (1) and harmalol (2) were converted by Rhodotorula rubra ATCC 20129 into the tryptamines, 2-acetyl-3-(2-acetamidoethyl)-7-methoxyindole (3) and 2-acetyl-3-(2-acetamidoethyl)-7-hydroxyindole (4), respectively. Harman (5) was biotransformed by Cunninghamella echinulata NRRL 3655 into 6-hydroxyharman (6) and harman-2-oxide (7).

authors

Herath W,Mikell JR,Ferreira D,Khan IA

doi

10.1248/cpb.51.646

subject

Has Abstract

pub_date

2003-06-01 00:00:00

pages

646-8

issue

6

eissn

0009-2363

issn

1347-5223

journal_volume

51

pub_type

杂志文章
  • Study on colon-specific 5-Fu pH-enzyme Di-dependent chitosan microspheres.

    abstract::Colon-specific drug delivery systems (CDDS) can improve the bioavailability of drug through the oral route. A novel formulation for oral administration using pH-enzyme Di-dependent chitosan mcirospheres (MS) and 5-Fu as a model drug has been investigated for colon-specific drug delivery by the emulsification/chemical ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.56.963

    authors: Zhao XL,Li KX,Zhao XF,Pang DH,Chen DW

    更新日期:2008-07-01 00:00:00

  • Bioactive saponins and glycosides. VII. On the hypoglycemic principles from the root cortex of Aralia elata Seem.: structure related hypoglycemic activity of oleanolic acid oligoglycoside.

    abstract::The hypoglycemic component, elatoside E, was isolated from the root cortex of Aralia elata SEEM. (Araliaceae) together with elatoside F and eight known oleanolic acid glycosides, elatosides A and C, oleanolic acid 3-O-[alpha-L-arabinofuranosyl (1-->4)]-beta-D-glucopyranosiduronic acid, oleanolic acid 3-O-beta-D-glucop...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.44.1923

    authors: Yoshikawa M,Murakami T,Harada E,Murakami N,Yamahara J,Matsuda H

    更新日期:1996-10-01 00:00:00

  • Minor saponins from Tetrapanax papyriferum.

    abstract::Four new minor saponins, papyrioside LE-LH, were isolated from the leaves of Tetrapanax papyriferum, and their structures were determined on the basis of spectroscopic evidence. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.45.552

    authors: Mutsuga M,Kojima K,Saracoglu I,Ogihara Y

    更新日期:1997-03-01 00:00:00

  • N-Arylpiperazine-1-carboxamide derivatives: a novel series of orally active nonsteroidal androgen receptor antagonists.

    abstract::A novel series of N-arylpiperazine-1-carboxamide derivatives was synthesized and their androgen receptor (AR) antagonist activities and in vivo antiandrogenic properties were evaluated. Reporter assays indicated that trans-2,5-dimethylpiperazine derivatives are potent AR antagonists, and in this series trans-N-4-[4-cy...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.53.402

    authors: Kinoyama I,Taniguchi N,Kawaminami E,Nozawa E,Koutoku H,Furutani T,Kudoh M,Okada M

    更新日期:2005-04-01 00:00:00

  • The practical synthesis of a uterine relaxant, bis(2-[[(2S)-2-([(2R)-2-hydroxy-2-[4-hydroxy-3-(2-hydroxyethyl)-phenyl]ethyl]amino)-1,2,3,4-tetrahydronaphthalen-7-yl]oxy]-N,N-dimethylacetamide) sulfate (KUR-1246).

    abstract::The synthetic route for a uterine relaxant, bis(2-[[(2S)-2-([(2R)-2-hydroxy-2-[4-hydroxy-3-(2-hydroxyethyl)-phenyl]ethyl]amino)-1,2,3,4-tetrahydronaphthalen-7-yl]oxy]-N,N-dimethylacetamide) sulfate (KUR-1246), was established by the coupling of optically active components, the bromohydrin 14 and the amine 24. We now d...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.49.1018

    authors: Yanagi T,Kikuchi K,Takeuchi H,Ishikawa T,Nishimura T,Yamamoto I

    更新日期:2001-08-01 00:00:00

  • Proton nuclear magnetic resonance study on the aromatic amino acid-guanine nucleotide system: effect of base methylation on the stacking interaction with tyrosine and phenylalanine.

    abstract::The stacking interactions of tyrosine methylester (TyrOMe)-guanosine-5'-monophosphate (GMP), TyrOMe-7-methylguanosine-5'-monophosphate (m7GMP), phenylalanine methylester (PheOMe)-GMP and PheOMe-m7GMP pairs in neutral buffer solution have been studied by proton nuclear magnetic resonance (1H-NMR). The H8 proton signal ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.37.1

    authors: Ishida T,Ohnishi K,Doi M,Inoue M

    更新日期:1989-01-01 00:00:00

  • Effect of glutathione on lambda deoxyribonucleic acid strand breaks in the reaction system of glutathione-alloxan in the presence of Fe(3+)-ethylenediaminetetraacetic acid.

    abstract::Alkaline sucrose density gradient and agarose gel electrophoresis methods were used to observe lambda deoxyribonucleic acid (DNA) strand breaks by the reaction system of reduced glutathione (GSH) with alloxan in the presence of Fe(3+)-ethylenediaminetetraacetic acid (EDTA). When DNA was incubated in the reaction syste...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.40.2147

    authors: Sakurai K,Haga K,Ogiso T

    更新日期:1992-08-01 00:00:00

  • In-die evaluation of capping tendency of pharmaceutical tablets using force-displacement curve and stress relaxation parameter.

    abstract::A novel in-die evaluation method of tablet capping tendency was proposed based on a force-displacement curve and stress relaxation parameter in a tableting process. In our previous study (Chem. Pharm. Bull., 59, 2011, Nakamura et al.), the phase diagram consisting of elastic recovery energy (E(e)) and plastic deformat...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.60.772

    authors: Nakamura H,Sugino Y,Watano S

    更新日期:2012-01-01 00:00:00

  • Further studies on new furostanol saponins from the bulbs of Allium macrostemon.

    abstract::Further studies by means of preparative HPLC led to the isolation of two new furostanol saponins, macrostemonoside J (1) and L (3), along with an artifact, macrostemonoside K (2) from the bulbs of Allium macrostemon. On the basis of chemical evidence and spectral analysis (1H-, 13C-NMR and FAB-MS), the structure of 1 ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.42.2180

    authors: Peng J,Yao X,Okada Y,Okuyama T

    更新日期:1994-10-01 00:00:00

  • Hapten synthesis for (+)-6-(2-chlorophenyl)-3-cyclopropanecarbonyl-8,11-dimethyl-2,3,4,5-tet rahydro-8H-pyrido[4',3':4,5]thieno[3,2-f] triazolo[4,3-a][1,4]diazepine (E6123).

    abstract::(+)-6-(2-Chlorophenyl)-3-cyclopropanecarbonyl-8,11-dimethyl-2,3,4, 5-tetrahydro-8H-pyrido[4',3':4,5]thieno[3,2-f]triazolo[4,3-a] [1,4]diazepine (E6123) is a very potent platelet-activating factor (PAF) receptor antagonist and shows potent anti-PAF activities at the microgram level in a variety of animal models. In ord...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.40.762

    authors: Miyazawa S,Okano K,Kawahara T,Machida Y,Yamatsu I

    更新日期:1992-03-01 00:00:00

  • Quantitative Analysis of Salidroside and p-Tyrosol in the Traditional Tibetan Medicine Rhodiola crenulata by Fourier Transform Near-Infrared Spectroscopy.

    abstract::A nondestructive, efficient, and rapid method for quantitative analysis of two bioactive components (salidroside and p-tyrosol) in Rhodiola crenulata, a traditional Tibetan medicine, by Fourier transform near-infrared (FT-NIR) spectroscopy was developed. Near-infrared diffuse reflectance spectra in the range of 4000 t...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c15-00558

    authors: Li T,He X

    更新日期:2016-01-01 00:00:00

  • Synthesis and pharmacological activity of 4-amino-5-chloro-2-methoxy-N-[(2S,4S)-1-ethyl-2-hydroxymethyl-4- pyrrolidinyl]benzamide (TKS159) and its optical isomers.

    abstract::Of 4-amino-5-chloro-2-methoxy-N-(1-ethyl-2-hydroxymethyl-4- pyrrolidinyl)benzamide, four optical isomers, (2S,4S)-1 (TKS159), (2S,4R)-25, (2R,4S)-26 and (2R,4R)-27, were prepared from optically active 4-amino-1-ethyl-2-hydroxymethylpyrrolidine di-p-toluenesulfonate [(2S,4S)-14, (2S,4R)-17, (2R,4S)-20 and (2R,4R)-23, r...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.47.1650

    authors: Yanagi T,Kitajima A,Anzai K,Kodama K,Mizoguchi J,Fujiwara H,Sakiyama H,Kamoda O,Kamei C

    更新日期:1999-11-01 00:00:00

  • Transport of harman alkaloids across Caco-2 cell monolayers.

    abstract::This study examined the intestinal transport of five harman alkaloids using the Caco-2 cell monolayer as a model of the human intestinal mucosa. Transport parameters, permeability coefficients and percent transports, were calculated and compared under identical conditions with atenolol. Permeability coefficients were ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.52.394

    authors: Khan SI,Abourashed EA,Khan IA,Walker LA

    更新日期:2004-04-01 00:00:00

  • Inner-hydrogen tautomerism in some 5,15-unsymmetrically disubstituted and beta-unsubstituted porphyrins.

    abstract::5,15-Unsymmetrically disubstituted and beta-unsubstituted porphyrins such as 5-R, 15-(3,5-dimethoxyphenyl) porphyrins [where R=2-benzyloxy-1-naphthyl (1), 2-(2-naphthylmethoxy)-1-naphthyl (2), anthryl (3), or 2,4,6-triphenylphenyl (4)] and 5-(2-benzyloxy-1-naphthyl), 10,15,20-tri(3,5-dimethoxyphenyl) porphyrin (1') we...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.56.1041

    authors: Tohara A,Sato M

    更新日期:2008-07-01 00:00:00

  • Antioxidant constituents of Caragana tibetica.

    abstract::Caragana tibetica KOM. (Fabaceae) is a medicinal plant that has been traditionally used in western part of China. In the course of our screening study on antioxidant activity of medicinal plants, the 70% acetone extract of the stems of C. tibetica was found to have a potent superoxide anion scavenging activity. Tibeti...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.53.1204

    authors: Xiang T,Uno T,Ogino F,Ai C,Duo J,Sankawa U

    更新日期:2005-09-01 00:00:00

  • Antitumor activity of Pulsatilla koreana saponins and their structure-activity relationship.

    abstract::Seventeen saponins isolated from the root of Pulsatilla koreana were examined for their in vitro cytotoxic activity against the human solid cancer cell lines, A-549, SK-OV-3, SK-MEL-2, and HCT15, using the SRB assay method, and their in vivo antitumor activity using BDF1 mice bearing Lewis lung carcinoma (LLC). The sa...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.53.1451

    authors: Bang SC,Lee JH,Song GY,Kim DH,Yoon MY,Ahn BZ

    更新日期:2005-11-01 00:00:00

  • Synthesis of BMS-309403-related compounds, including [¹⁴C]BMS-309403, a radioligand for adipocyte fatty acid binding protein.

    abstract::Adipocyte fatty acid binding protein (A-FABP; FABP4), which is predominantly expressed in macrophages and adipose tissue, regulates fatty acid storage and lipolysis, and is also an important mediator of inflammation. Here, we report a synthesis of (14)C-labeled 2-[2'-(5-ethyl-3,4-diphenyl-1H-pyrazol-1-yl)biphenyl-3-yl...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.60.164

    authors: Okada T,Hiromura M,Otsuka M,Enomoto S,Miyachi H

    更新日期:2012-01-01 00:00:00

  • Inducer-specific regulators of tumor necrosis factor alpha production.

    abstract::Novel potent regulators of tumor necrosis factor alpha (TNF-alpha) production by a human promyelocytic leukemia cell line, HL-60, were prepared. All the compounds showed inducer-specific and bidirectional regulation of TNF-alpha production, i.e., they enhanced 12-O-tetradecanoylphorbol-13-acetate-induced TNF-alpha pro...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.44.1980

    authors: Miyachi H,Azuma A,Hioki E,Kobayashi Y,Iwasaki S,Hashimoto Y

    更新日期:1996-10-01 00:00:00

  • Cardiac glycosides from Erysimum cheiranthoides.

    abstract::Three new cardiac glycosides named cheiranthoside VIII (1), cheiranthoside IX (2) and cheiranthoside X (3) were isolated from the seeds of Erysimum cheiranthoides. Based on spectroscopic data, the structures of 1-3 were characterized as strophanthidin 3-O-beta-D-glucopyranosyl-(1-->4)-beta-D-antiaropyranoside, cheiran...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.50.861

    authors: Lei ZH,Nakayama H,Kuniyasu A,Tai BS,Nohara T

    更新日期:2002-06-01 00:00:00

  • New progesterone esters as 5alpha-reductase inhibitors.

    abstract::The pharmacological activity of four new progesterone derivatives: 4-bromo-17alpha-(p-fluorobenzoyloxy)-4-pregnene-3,20-dione (7), 4-bromo-17alpha-(p-bromobenzoyloxy)-4-pregnene-3,20-dione (8), 4-bromo-17alpha-(p-chlorobenzoyloxy)-pregnene-3,20-dione (9) and 4-bromo-17alpha-(p-toluoyloxy)-4-pregnene-3,20-dione (10) wa...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.49.1081

    authors: Cabeza M,Heuze I,Bratoeff E,Murillo E,Ramirez E,Lira A

    更新日期:2001-09-01 00:00:00

  • Tandem enzymatic resolution yielding L-alpha-aminoalkanedioic acid omega-esters.

    abstract::The tandem action of serine protease (alpha-chymotrypsin or subtilisin BPN') and Aspergillus genus aminoacylase on racemic N-acetyl-alpha-aminoalkanedioic acid alpha,omega-diester produced L-alpha-aminoalkanedioic acid omega-ester in good yield and high optical purity. L-alpha-Aminosuberic acid omega-ester thus obtain...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.44.212

    authors: Nishino N,Arai T,Ueno Y,Ohba M

    更新日期:1996-01-01 00:00:00

  • Preparation and Evaluation of Stomatitis Film Using Xyloglucan Containing Loperamide.

    abstract::Stomatitis induced by radiation therapy or cancer chemotherapy is a factor in sleep disorders and/or eating disorders, markedly decreasing patient quality of life. In recent years, disintegrating oral films that are easy to handle have been developed; therefore, we focused on the formulation of these films. We prepare...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c15-00926

    authors: Kawano Y,Sasatsu M,Mizutani A,Hirose K,Hanawa T,Onishi H

    更新日期:2016-06-01 00:00:00

  • Functional analysis of the iron(II) etiocorrphycene incorporated in the myoglobin heme pocket.

    abstract::The iron(III) complex of 2,7,12,17-tetraethyl-3,6,11,18-tetra-methylcorrphycene, an isomeric heme, was complexed with apomyoglobin to examine the ligand binding ability of the novel macrocycle under physiological conditions. The reconstituted holoprotein was found to be functionally active at pH 7.4 and 20 degrees C a...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.49.345

    authors: Neya S,Nakamura M,Imai K,Funasaki N

    更新日期:2001-03-01 00:00:00

  • Fasciculic acids A, B and C as calmodulin antagonists from the mushroom Naematoloma fasciculare.

    abstract::Three new fasciculol esters, fasciculic acids A (1), B (2) and C (3), having potent calmodulin antagonistic activity were isolated from the toxic mushroom Naematoloma fasciculare (Fr.) Karst. Their structures were elucidated on the basis of spectral and chemical evidence. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.37.3247

    authors: Takahashi A,Kusano G,Ohta T,Ohizumi Y,Nozoe S

    更新日期:1989-12-01 00:00:00

  • Aglaiabbrevins A-D, New Prenylated Bibenzyls from the Leaves of Aglaia abbreviata with Potent PTP1B Inhibitory Activity.

    abstract::Four new prenylated bibenzyls, named aglaiabbrevins A-D (2, 4-6), were isolated from the leaves of Aglaia abbreviata, along with two known related analogues, 3,5-dihydroxy-2-[3,7-dimethyl-2(E),6-octadienyl]bibenzyl (7) and 3,5-dihydroxy-2-(3-methyl-2-butenyl)bibenzyl (8). The structures of the new compounds were eluci...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c16-00868

    authors: Sun P,Jiang CS,Zhang Y,Liu AH,Liang TJ,Li J,Guo YW,Jiang JM,Mao SC,Wang B

    更新日期:2017-01-01 00:00:00

  • Application of the Lewis acid-Lewis base bifunctional asymmetric catalysts to pharmaceutical syntheses: stereoselective chiral building block syntheses of human immunodeficiency virus (HIV) protease inhibitor and beta3-adenergic receptor agonist.

    abstract::Chiral building block syntheses of promising drugs were achieved using two types of catalytic stereoselective cyanosilylations of aldehydes promoted by Lewis acid-Lewis base bifunctional catalysts 1 and 2 as the key steps (diastereoselective cyanosilylation of amino aldehyde and enantioselective cyanosilylation). In t...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.51.702

    authors: Nogami H,Kanai M,Shibasaki M

    更新日期:2003-06-01 00:00:00

  • Indonesian medicinal plants. IX. Chemical structures of gongganosides A, B, and C, three new quinovic acid glycosides from the bark of Bhesa paniculata (Celastraceae).

    abstract::Three new quinovic acid glycosides, named gongganosides A (1), B (2), and C (3), were isolated from the bark of Bhesa paniculata (Celastraceae), an Indonesian medicinal plant collected in Sumatra Island. The chemical structures have been elucidated on the basis of chemical and physicochemical evidence as quinovic acid...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.42.1596

    authors: Ohashi K,Kojima H,Tanikawa T,Okumura Y,Kawazoe K,Tatara N,Shibuya H,Kitagawa I

    更新日期:1994-08-01 00:00:00

  • Scale-up of high shear granulation based on the internal stress measurement.

    abstract::Scale-up of wet granulation in a vertical high shear mixer was conducted. Pharmaceutical excipient powders composed of lactose, cornstarch and micro-crystallinecellulose, and hydroxypropylcellulose as a binder were mixed together and then granulated with purified water under various operating conditions and vessel sca...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.53.351

    authors: Watano S,Okamoto T,Sato Y,Osako Y

    更新日期:2005-04-01 00:00:00

  • Synthesis of an immunologically active fragment analog of prothymosin alpha with enhanced enzymatic stability.

    abstract::A fragment analog, [D-Arg30]prothymosin alpha fragment 1-30, containing D-arginine in place of arginine residue at position 30 was synthesized by the liquid phase procedure and studied for immunological effect on the impaired blastogenic response of T-lymphocytes isolated from uremic patients after treatment of human ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.39.752

    authors: Abiko T,Sekino H

    更新日期:1991-03-01 00:00:00

  • Catalytic Asymmetric 1,3-Dipolar Cycloaddition of α,β-Unsaturated Amide and Azomethine Imine.

    abstract::α,β-Unsaturated amides were incorporated as viable dipolarophiles in a catalytic asymmetric 1,3-dipolar cycloaddition of azomethine imines. The use of a 7-azaindoline auxiliary was essential to acquire sufficient reactivity with excellent diastereoselectivity, likely due to the chelating activation of the amide by the...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c20-00130

    authors: Li Z,Kumagai N,Shibasaki M

    更新日期:2020-01-01 00:00:00